Diisopropylethylamine → N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4nitro-L-phenylalanine methyl ester

HRID 1018134Notes

Reaction equation

HRID 1018134 reaction equation
Cl.[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH2:6].[N:18]([CH2:21][CH2:22][C:23]1([C:28](O)=[O:29])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[N+:19]=[N-:20].F[P-](F)(F)(F)(F)F.N1(O[P+](N(C)C)(N(C)C)N(C)C)C2C=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>ClCCl.CN(C=O)C.O.C(OCC)(=O)C.CCCCCC>[CH3:2][O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][CH:9]=1)[NH:6][C:28]([C:23]1([CH2:22][CH2:21][N:18]=[N+:19]=[N-:20])[CH2:27][CH2:26][CH2:25][CH2:24]1)=[O:29]

Participants

10

Reactant 4

HCID 81531DiisopropylethylamineHCID 151348Benzotriazol-1-yloxy-tris(dimethylamino)phosphonium hexafluorophosphateHCID 11715866Methyl 4-nitro-L-phenylalaninate hydrochlorideHCID 226601251-(2-Azidoethyl)cyclopentanecarboxylic acid

Product 1

HCID 12042583N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4nitro-L-phenylalanine methyl esterYield 95.1%

Reagents, catalysts & solvents 5

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 4-nitro-L-phenylalanine methyl ester hydrochloride (3.0 g, 11.5 mmol), 1-(2-azidoethyl)cyclopentane carboxylic acid (2.3 g, 12.7 mmol) and BOP (5.34 g, 12.1 mmol) in dichloromethane (6 mL) and DMF (4 mL) was treated with diisopropylethylamine (4.2 mL, 24.2 mmol). The mixture was stirred overnight at which time TLC (1:1 hexane:ethyl acetate) indicated no more starting material. The mixture was diluted with water, extracted with ethyl acetate. The extracts were washed with water and brine, then were dried (Na2SO4), filtered and evaporated in vacuo. The residue was purified by chromatography over silica gel (3:1 hexane:ethyl acetate) to afford 4.26 g of N-[[1-(2-azidoethyl)cyclopentyl]carbonyl]-4-nitro-L-phenylalanine methyl ester.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed with water and brine
  3. dry with materialwere dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified by chromatography over silica gel (3:1 hexane:ethyl acetate)

Sources & evidence

ORD record
ord-31b220c790b040cc9630e34cbc648af3
Source dataset
uspto-grants-2002_11
Patent number
US06479666B2

Reaction notes

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